Woolford Vacation Packages

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Your Woolford Vacation

Say bye-bye to the stress of planning and hello to a Woolford vacation package. With the finer details organized before you go, you can focus on discovering every inch of this city, starting with Downtown Cambridge, which is good for bars and pubs, culture and cafes. In the mood for a bit of sightseeing? A trip to Woolford wouldn't be complete without checking out Harriet Tubman Underground Railroad National Historical Park, Spocott Windmill and other major attractions. Your ideal Woolford vacation is just clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored just for you.

Top Woolford Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was CA $2,372, price is now CA $1,877 per person
CA $1,877
per person
Sep 3 - Sep 8
found 2 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
8.8/10 Excellent! (2,496 reviews)

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Price was CA $3,431, price is now CA $2,583 per person
CA $2,583
per person
Sep 24 - Sep 27
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
6.6/10 (23 reviews)
A diamond in the rough! Not pristine or glamorous and a little outdated, but it worked for a quick 3 day get away trip. The beds were very comfortable so it was easy to look past the outdated cosmetics of the room and bathroom. Love love love the location! It is absolutely perfect if you have small kids and want to be near the fun attractions OC has to offer. We have stayed here a few times and would definitely book again! Also, I really loved how they booked families with children all on one floor. It made for very peaceful nights without ruckus waking anyone up at 2am. 10/10 recommend if you aren't picky about the most up to date interior.

Reviewed on Jul 20, 2026

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was CA $4,217, price is now CA $3,303 per person
CA $3,303
per person
Sep 24 - Sep 27
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
8.2/10 Very good! (749 reviews)
Parking was a 1-2 blocks away. The spots were so tight the passenger had to get out before parking. Coffee pots were small and very dirty. Desk people were nice. It’s old but clean.

Reviewed on Jul 19, 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was CA $2,537, price is now CA $1,989 per person
CA $1,989
per person
Sep 3 - Sep 8
found 6 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
9.4/10 Exceptional! (795 reviews)
Modern, clean, well-kept, comfy, quiet, close to beach.

Reviewed on Jul 19, 2026

Monte Carlo Boardwalk Oceanfront Ocean City

Monte Carlo Boardwalk Oceanfront Ocean City

3 out of 5
Downtown Ocean City
Price was CA $2,435, price is now CA $1,934 per person
CA $1,934
per person
Sep 3 - Sep 8
found 1 hour ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
8.2/10 Very good! (1,000 reviews)

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Woolford Hotel Deals

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
9.6/10 Exceptional! (34 reviews)
"We you this place for the groomsmen’s house and it was perfect! They allow multiple cars to be parked I. The driveway which is super helpful especially when you have multiple people coming from different places. The kitchen and table was excellent we were able to sit everyone around the table and ..."

Reviewed on Jul 2, 2026

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The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted

Woolford MD
9.8/10 Exceptional! (78 reviews)
"If you're looking for a relaxing getaway with quite surroundings and privacy, then this is the place for you. Property description in accurate. Owner is super helpful and laid back. Check in and check out policies are clearly listed and very reasonable, nothing out of the ordinary. FIVE stars across ..."

Reviewed on Jul 7, 2026

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Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is CA $421 per night from Jul 29 to Jul 30
CA $421
CA $545 total
Jul 29 - Jul 30
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Loved staying here and can't wait to come back. It's perfect for a girls' weekend, couples' weekend or with kids. I've been in the fall and summer and looking forward to making another visit."

Reviewed on Jul 20, 2026

Hyatt Regency Chesapeake Bay
See all 547 properties in Woolford
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Woolford attractions

Woods Island

Commune with nature and explore the great outdoors at Woods Island during your travels in Woolford.
See properties

Frequently asked questions

How much does a Woolford vacation package cost?
You'll find cheap prices from CA $1,877 on Expedia for your Woolford break. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Woolford costs.
What are the cheapest months to go to Woolford?
Travel in the shoulder or low season and you're likely to get cheap Woolford vacation packages. Keep in mind that public holidays and major local events can impact prices, so do a little research before booking.
How many days is enough for Woolford?
With a well-organized travel plan, you can easily visit the top Woolford sights in a few days. But if you want to discover hidden gems or take day trips, think about booking your Woolford vacation for longer.
How to find the best Woolford package deals?
Use Expedia's filters to help you find some unbeatable Woolford package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Woolford package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Woolford vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging accommodations and flights separately. Better still, you can customize your Woolford trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Woolford?
If you've got your Woolford vacation dates finalized, book as soon as you can to grab some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Woolford?

  1. Choose when to go: Check your schedule and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to escape to Woolford.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to experiences and flights. Your accommodations will likely be the largest expense during your trip to Woolford.
  3. Decide how long to go for: Now that you know more about Woolford, you can work out the ideal length of your vacation. Put together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a Woolford vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.